Polyhydroxy stilbenes compound preparation and uses as drugs for suppressing SARS

A polyhydroxystilbene compound technology, which is applied in the field of preparation of polyhydroxystilbene compounds and the use of drugs for inhibiting SARS virus, can solve the problem of undetected SARS-CoV effect

Inactive Publication Date: 2007-08-15
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, SANP did not detect an effect on SARS-CoV

Method used

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  • Polyhydroxy stilbenes compound preparation and uses as drugs for suppressing SARS
  • Polyhydroxy stilbenes compound preparation and uses as drugs for suppressing SARS
  • Polyhydroxy stilbenes compound preparation and uses as drugs for suppressing SARS

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] (E)-2-[2-(3,5-dihydroxyphenyl)vinyl]-3,5-dimethyl-4-hydroxypyridine; (also known as: (E)-4,6-dimethyl base-3',5,5'-trihydroxystilbene-2-nitrogen)

[0107] Synthesis of 3,5-dimethyl-4-methoxypyridine-2-methylphosphonate: 2-chloromethyl-3,5-dimethyl-4-methoxypyridine was added to a 50mL three-neck flask (0.01mol), 2.5g (0.016mol) of triethyl phosphite, a small amount of tetrabutylammonium iodide, stir, heat in an oil bath to 100-110°C, and react for 3-6h. The reactant was distilled under reduced pressure below 90°C to remove excess triethyl phosphite, and the remaining light orange-red sticky matter in the bottle was directly used for the next reaction.

[0108] Synthesis of (E)-2-[2-(3,5-dimethoxyphenyl) vinyl]-3,5-dimethyl-4-methoxypyridine: the phosphonate solution obtained in the previous step reaction In 50 mL of dry tetrahydrofuran (THF), cool in an ice-salt bath to below 0°C, quickly add NaH powder (0.025 mol) under stirring, and stir for 30 min. With stirring, ...

Embodiment 2

[0111] (E)-2-[2-(4-hydroxyphenyl)vinyl]-3,5-dimethyl-4-hydroxypyridine (also known as: (E)-4,6-dimethyl-4, 5'-dihydroxystilbene-2-nitrogen)

[0112] Synthesis of 3,5-dimethyl-4-methoxypyridine-2-methylphosphonate: 2-chloromethyl-3,5-dimethyl-4-methoxypyridine was added to a 50mL three-neck flask (0.01mol), triethyl phosphite 2.5g (0.016mol), a small amount of tetrabutylammonium iodide, stirred, heated in an oil bath to 100-110°C, and reacted for 3-6h. The reactant was distilled under reduced pressure below 90°C to remove excess triethyl phosphite, and the remaining light orange-red sticky matter in the bottle was directly used for the next reaction.

[0113] Synthesis of (E)-2-[2-(4-methoxyphenyl)vinyl]-3,5-dimethyl-4-methoxypyridine: the phosphonate obtained in the previous step reaction was dissolved in 50 mL and dried In tetrahydrofuran (THF), cool in an ice-salt bath to below 0°C, add NaH powder (0.025mol) rapidly under stirring, and stir for 30min. With stirring, 30 mL...

Embodiment 3

[0116] (E)-2-[2-(2,5-dihydroxyphenyl)vinyl]-3,5-dimethyl-4-hydroxypyridine (also known as: (E)-4,6-dimethyl -2,5,5'-trihydroxystilbene-2-nitrogen)

[0117] Synthesis of 3,5-dimethyl-4-methoxypyridine-2-methylphosphonate: 2-chloromethyl-3,5-dimethyl-4-methoxypyridine was added to a 50mL three-neck flask (0.01mol), triethyl phosphite 2.5g (0.016mol), a small amount of tetrabutylammonium iodide, stirred, heated in an oil bath to 100-110°C, and reacted for 3-6h. The reactant was distilled under reduced pressure below 90°C to remove excess triethyl phosphite, and the remaining light orange-red sticky matter in the bottle was directly used for the next reaction.

[0118] Synthesis of (E)-2-[2-(2,5-dimethoxyphenyl) vinyl]-3,5-dimethyl-4-methoxypyridine: the phosphonate solution obtained in the previous step reaction In 50 mL of dry tetrahydrofuran (THF), cool in an ice-salt bath to below 0°C, quickly add NaH powder (0.025 mol) under stirring, and stir for 30 min. With stirring, 30...

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PUM

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Abstract

The invention provides a group of polyhydroxy stilbene compounds, their preparing process and use for suppressing and eradicating SARS coronavirus. The preparing process comprises, preparing phosphonic ester by reacting multi-alkyl substituted chloro (bromo) methoxyl or pyridine compounds with triethyl phosphate, then reacting phosphonate ester compound with multi-alkyl (oxy) phenylpyridine methyl aldehyde to obtain multi-alkyl (oxy) stilbene compounds. Finally acting with boron tribromide to obtain polyhydroxy stilbene compounds with substituent groups.

Description

technical field [0001] The invention relates to a new class of medicinal polyhydroxystilbene compounds, a preparation method and application thereof. This new compound is used for inhibiting and killing SARS coronavirus. Background technique [0002] Stilbene compounds are a general term for a class of compounds with a stilbene core. In nature, polyhydroxy stilbene compounds are found in many Chinese herbal medicines such as Veratrum, Rhubarb, Huzhang, Shouwu, etc., and in foods such as grapes, peanuts, and mulberries. , Improving immunity and many other physiological activities. [0003] In WO 02 / 057219 patent, a class of stilbene compounds are disclosed as regulators of T cells, neutrophils, macrophages and corresponding cytokines for the treatment of immune, inflammatory and autoimmune diseases. In the structure disclosed in the WO02 / 057219 patent, only one benzene ring contains alkoxy or hydroxyl substituents at the 3 and 5 positions, the other benzene ring is basical...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/06C07D213/28C07D213/62C07C39/21C07C37/00C07C43/253A61K31/44A61K31/075A61K31/05A61K9/20A61K9/00A61P31/14A61P11/00
Inventor 赵伟杰李泽琳孟庆伟温瑞兴王世盛曾毅李悦青
Owner DALIAN UNIV OF TECH
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